The Philosophical Investor's Blog

From Inversion to Aspiration: Choosing Vitality Over Comfort

Charlie Munger Inversion to Aspiration

Last week, my reflections were guided by Charlie Munger’s favorite mental model: inversion.

Rather than asking how to design a good life, the question was simpler and sterner: What does a bad life look like—and how might we avoid it?

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How I Won a Tennis Tournament by Doing Less, Not More

challenges winning tennis doubles

I recently won my first doubles tennis tournament in a few years. This was the most satisfying because we won four matches on three surfaces, with one of the battles being quite challenging, requiring a come-from-behind victory.

Gary Carmell won his first Doubles title April 2026

It took longer than I expected—and probably longer than I wanted—but in retrospect,

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A Date with Success

Fear of Success
“Watch out, you might get what you’re after.”

The line floats through Burning Down the House almost as a warning—half playful, half ominous. I’ve heard it countless times, usually sung along to without much thought. But lately, it’s been echoing differently.

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Playing in Our Own Plays

Playing in Our Own Plays

Barcelona, the zoo, clay courts, and the art of living awake

We were in Barcelona—intentionally and accidentally at the same time.

Heather and I arrived after spending the prior week at the Rolex Monte‑Carlo Open,

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Trade-Offs in Monte Carlo

Monte Carlo Heather and Gary Carmell

Sometimes the Place Trumps the Play
On Trade‑Offs, Tennis, and the Economics of Time

Thomas Sowell famously defined economics not as money, markets, or math, but as the allocation of scarce resources that have alternative uses.

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The Mind Is in Every Cell — An Investor’s Reflection

embodied investing

After finishing listening to Sound Man on Audible, which is a book I highly recommend for music lovers, it cycles through snippets of other books the algorithm thinks I might like. One of those books was The Uncool by Cameron Crowe.

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Pattern Recognition Is Not Prophecy

energy geopolitics
On Energy, Empire, and the Seductive Power of Coherent Stories

One of the most intoxicating human capacities is pattern recognition.

It is the engine of intelligence, the source of insight, and the reason we survive complexity at all. But it is also the birthplace of our most confident errors—especially when patterns begin to feel inevitable.

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Houston - Gaining Energy?

Houston Oil Energy

Last week was quite busy, so for this post, I decided to turn to Copilot to help me produce the output. Over the past year, our acquisitions at CWS have been heavily concentrated on properties in the Houston area. Of course,

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Hot and Hotter

Housing

I wanted to return to the subject of housing and share some of the latest graphs related to the single-family and multifamily markets. I’ll start with the single-family sector.

Demand continues to be strong but it has decelerated from the torrid Covid-catalyzed pace of 2020.

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How To Find Satisfaction in Retirement

Happy Retirement

With the baby boomers starting to descend down the other side of the hill with millions soon following, retirement planning has understandably become not only very important but big business as well. Most of what future retirees and financial advisors focus on are how to prepare financially so that not only can people have the choice to retire but once they do they don’t outlive their money.

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